The synthesis of BODIPY dyes is typically achieved by one of two different one-pot procedures (Scheme 1) [1,2]: (a) Lewis acid (usually trifluoroacetic acid, TFA) catalyzed condensation between a 2-substituted pyrrole and an aldehyde, followed by oxidation with DDQ or p-chloranil, and subsequent treatment with base (Et …
How does BODIPY work?
BODIPY and many of its derivatives have received attention recently for being fluorescent dyes with unique properties. They strongly absorb UV-radiation and re-emit it in very narrow frequency spreads, with high quantum yields, mostly at wavelengths below 600 nm.
What is BODIPY staining?
With its nonpolar structure and long-wavelength absorption and fluorescence, BODIPY® 493/503 can be used as a stain for neutral lipds and as a tracer for oil and other nonpolar lipids.
Is BODIPY a fluorescent?
Invitrogen BODIPY FL dye is a bright, green-fluorescent dye with similar excitation and emission to fluorescein (FITC) or Invitrogen Alexa Fluor 488 dye. It has a high extinction coefficient and fluorescence quantum yield and is relatively insensitive to solvent polarity and pH change.
Is bodipy aromatic?
3. BODIPYs fused to aromatic heterocycles. So far, instead of aromatic hydrocarbons, many aromatic ring-fused BODIPY dyes have been developed by introducing 5-membered aromatic heterocycles, such as furan, thiophene and pyrrole derivatives, at the b bond, as summarized in Fig.
Is BODIPY cell permeable?
To test our hypothesis, we chose boron-dipyrromethene (BODIPY) as the model fluorescent dye in our study. … However, BODIPY indeed suffer problems of low-water solubility and poor membrane permeability 27 , 28.
Can BODIPY be fixed?
We routinely add BODIPY 493/503 from a 1 mg/ml stock to fixed or living cells at a final concentration of 1 μg–10 μg/ml; followed by at least a 1-h incubation at 37°C. The final concentration of BODIPY 493/503 depends on fat droplet size, the larger the fat droplets, the less stain is needed.
Is BODIPY water soluble?
BODIPY dye (A) is highly water-soluble. … BODIPY dye A displays weak fluorescence in 0.5 M phosphate buffer solution (PBS) (pH 7.40) with fluorescence quantum yield of only 4.2% while it becomes highly fluorescent with fluorescence quantum yields of 68% and 61% in methylene chloride and ethanol, respectively.
What is Nile red used for?
Nile red is used to localize and quantitate lipids, particularly neutral lipid droplets within cells.
Is Nile Red Polar?
Nile red is an uncharged hydrophobic molecule whose fluorescence is strongly influenced by the polarity of its environment. It interacts with many, but not all, native proteins, including beta-lactoglobulin, kappa-casein, and albumin, with a wide range of spectral changes for different proteins.
Is Nile red fluorescent?
Nile red exhibits properties of a near-ideal lysochrome. It is strongly fluorescent, but only in the presence of a hydrophobic environment. The dye is very soluble in the lipids it is intended to show, and it does not interact with any tissue constituent except by solution.
Is BODIPY polar?
BODIPYs show good stability both to environmental changes (such as pH [6]) and light [7]. Yet, due to the nonpolar nature of BODIPY core, they tend to aggregate in highly polar solvents [8].
How do you dissolve BODIPY?
Dissolve 1.3 mg BODIPY in 1 ml DMSO and can be stored at −20 °C. 2 μM BODIPY staining solution can be prepared by diluting stock solution 1:2,500 in PBS.
Is boron a fluorescent?
The boron fluorescence quantum yields are below to 1%, this is due to intramolecular rotation [16]. Thus, the dependence of the fluorescence quantum yield of ligand 1 and compound 2 on the viscous medium was studied using methanol and glycerol binary mixture.
What causes Stokes shift?
The Stokes shift is due to the fact that some of the energy of the excited fluorophore is lost through molecular vibrations that occur during the brief lifetime of the molecule’s excited state. This energy is dissipated as heat to surrounding solvent molecules as they collide with the excited fluorophore.
What is fluorescein sodium used for?
Fluorescein sodium, the sodium salt of fluorescein, is used extensively as a diagnostic tool in the field of ophthalmology and optometry, where topical fluorescein is used in the diagnosis of corneal abrasions, corneal ulcers and herpetic corneal infections.
What is FRET analysis?
The technique of fluorescence resonance energy transfer (more commonly referred to by the acronym FRET), when applied to optical microscopy, permits determination of the approach between two molecules within several nanometers (see Figure 1), a distance sufficiently close for molecular interactions to occur.
Does DMSO quench fluorescence?
The presence of dimethyl sulfoxide (DMSO) even in concentrations as low as 1% decreases the yield of fluorescence. Neglecting this quenching leads to the erroneous conclusion that DMSO in a concentration dependent manner inhibits the thapsigargin induced histamine release from peritoneal rat mast cells.
How does filipin bind to cholesterol?
Filipin is a naturally fluorescent polyene antibiotic that binds to cholesterol but not to esterified sterols. … Filipin fluorescence is observed with UV excitation around 360 nm and emission around 480 nm. Filipin binding perturbs the bilayer structure, so filipin cannot be used on living cells.
How do you detect lipid droplets?
Lipid droplets can be visualized either by staining the lipid ester core using fluorescent dyes or by labeling lipid droplet-specific proteins using antibodies.
Where are lipid droplets found?
adipose tissue Lipid droplets, also referred to as lipid bodies, oil bodies or adiposomes, are lipid-rich cellular organelles that regulate the storage and hydrolysis of neutral lipids and are found largely in the adipose tissue.
Is Nile red toxic?
TOXICITY AND IRRITATION NILE RED: No significant acute toxicological data identified in literature search. All waste must be handled in accordance with local, state and federal regulations.
Is Nile red Canadian?
residing in Montreal, Quebec, Canada. He runs the NileRed YouTube channel and social media accounts.
Is Nile Red Dead?
NileRed on Twitter: I’m not dead. I just severely underestimated how long it would take to move and build a new lab
Graduated from ENSAT (national agronomic school of Toulouse) in plant sciences in 2018, I pursued a CIFRE doctorate under contract with Sun’Agri and INRAE in Avignon between 2019 and 2022. My thesis aimed to study dynamic agrivoltaic systems, in my case in arboriculture. I love to write and share science related Stuff Here on my Website. I am currently continuing at Sun’Agri as an R&D engineer.